"Dear Mama" was released on February 21, 1995 as the first single for the album. The single was the most successful of all the singles released from the album. The song is considered by critics, fans, and purists as one of the greatest hip hop songs of all-time, and one of 2Pac's best songs in particular, being ranked number four on About.com's "Top 100 Rap Songs" list.
The "Dear Mama" music video was directed by Calvin Caday while 2Pac was incarcerated; thus, a Tupac look-alike had to be used for certain moments in the video. Afeni Shakur was also featured, shown flipping through pages of a photo album containing pictures of a younger Tupac. The video also shows snippets of articles relating to the Black Panthers, alluding to her past history as a member of this political organization.